Controlled synthesis of O-glycopolypeptide polymers and their molecular recognition by lectins

Biomacromolecules

Volumn 13, Issue 5, 2012, Pages 1287-1295

  Pati, Debasis ^a   Shaikh, Ashif Y ^a   Das, Soumen ^a   Nareddy, Pavan Kumar ^c   Swamy, Musti J ^c   Hotha, Srinivas ^b   Gupta, Sayam Sen ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

^b INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH   (India)

^c UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING PROCESS; CONTROLLED SYNTHESIS; ENTROPIC CONTRIBUTIONS; FACILE SYNTHESIS; GLYCOSYL DONORS; HELICAL STRUCTURES; HEMAGGLUTINATION ASSAYS; HIGH MOLECULAR WEIGHT; HIGH YIELD; ISOTHERMAL TITRATION CALORIMETRY; N-CARBOXYANHYDRIDE; SECONDARY CONFORMATION;

AMINO ACIDS; ANTIGEN-ANTIBODY REACTIONS; MOLECULAR RECOGNITION; STOICHIOMETRY;

POLYMERS;

AMINO ACID; LECTIN; O GLYCOPOLYPEPTIDE POLYMER; POLYMER; UNCLASSIFIED DRUG;

ALPHA HELIX; AQUEOUS SOLUTION; ARTICLE; BINDING KINETICS; ENTHALPY; GLYCATION; HEMAGGLUTINATION; ISOTHERMAL TITRATION CALORIMETRY; MOLECULAR RECOGNITION; POLYMERIZATION; PRECIPITATION; PRIORITY JOURNAL; STOICHIOMETRY; SYNTHESIS;

ANHYDRIDES; GLYCOPEPTIDES; LECTINS; MOLECULAR STRUCTURE; POLYMERIZATION; POLYMERS;

EID: 84861175987     PISSN: 15257797     EISSN: 15264602     Source Type: Journal    
DOI: 10.1021/bm201813s     Document Type: Article

References (61)

1. Godula, K.; Rabuka, D.; Nam, K.; Bertozzi, C. Angew. Chem., Int. Ed. 2009, 48, 4973-4976
2. Liu, S.; Maheshwari, R.; Kiick, K. L. Macromolecules 2009, 42, 3-13
3. Manning, D. D.; Hu, X.; Beck, P.; Kiessling, L. L. J. Am. Chem. Soc. 1997, 119, 3161-3162
4. Mortell, K. H.; Gingras, M.; Kiessling, L. L. J. Am. Chem. Soc. 1994, 116, 12053-12054
5. Prescher, J. A.; Bertozzi, C. R. Nat. Chem. Biol. 2005, 1, 13-21
6. Wang, Y.; Kiick, K. L. J. Am. Chem. Soc. 2005, 127, 16392-16393
7. Albertin, L.; Cameron, N. R. Macromolecules 2007, 40, 6082-6093
8. Chen, G.; Tao, L.; Mantovani, G.; Geng, J.; Nystróm, D.; Haddleton, D. M. Macromolecules 2007, 40, 7513-7520
9. Ladmiral, V.; Mantovani, G.; Clarkson, G. J.; Cauet, S.; Irwin, J. L.; Haddleton, D. M. J. Am. Chem. Soc. 2006, 128, 4823-4830
10. Ladmiral, V.; Melia, E.; Haddleton, D. M. Eur. Polym. J. 2004, 40, 431-449
11. Spain, S. G.; Gibson, M. I.; Cameron, N. R. J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 2059-2072
12. Ting, S. R. S.; Min, E. H.; Escalé, P.; Save, M.; Billon, L.; Stenzel, M. H. Macromolecules 2009, 42, 9422-9434
13. Gamblin, D. P.; Scanlan, E. M.; Davis, B. G. Chem. Rev. 2008, 109, 131-163
14. Seeberger, P. H.; Werz, D. B. Nature 2007, 446, 1046-1051
15. Ambrosi, M.; Cameron, N. R.; Davis, B. G. Org. Biomol. Chem. 2005, 3, 1593-1608
16. Ting, S. R. S.; Chen, G.; Stenzel, M. H. Polym. Chem. 2010, 1, 1392-1412
17. Mammen, M.; Choi, S.-K.; Whitesides, G. M. Angew. Chem., Int. Ed. 1998, 37, 2754-2794
18. Connolly, D. T.; Townsend, R. R.; Kawaguchi, K.; Bell, W. R.; Lee, Y. C. J. Biol. Chem. 1982, 257, 939-945
19. Weigel, P. H.; Oka, J. A. J. Biol. Chem. 1983, 258, 5095-5102
20. Weigel, P. H.; Yik, J. H. N. Biochim. Biophys. Acta 2002, 1572, 341-363
21. Cho, C. S.; Seo, S. J.; Park, I. K.; Kim, S. H.; Kim, T. H.; Hoshiba, T.; Harada, I.; Akaike, T. Biomaterials 2006, 27, 576-585
22. Deming, T. J. Soft Matter 2005, 1, 28-35
23. Lu, H.; Wang, J.; Bai1, Y.; Lang, J. W.; Liu, S.; Lin, Y.; Cheng, J. Nat. Commun. 2011, 2, 206-214
24. Deming, T. J. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 3011-3018
25. Hadjichristidis, N.; Iatrou, H.; Pitsikalis, M.; Sakellariou, G. Chem. Rev. 2009, 109, 5528-5578
26. Aoi, K.; Tsutsumiuchi, K.; Aoki, E.; Okada, M. Macromolecules 1996, 29, 4456-4458
27. Aoi, K.; Tsutsumiuchi, K.; Okada, M. Macromolecules 1994, 27, 875-877
28. Rüde, E.; Westphal, O.; Hurwitz, E.; Fuchs, S.; Sela, M. Immunochemistry 1966, 3, 137-151
29. Tsutsumiuchi, K.; Aoi, K.; Okada, M. Macromolecules 1997, 30, 4013-4017
30. Kramer, J. R.; Deming, T. J. J. Am. Chem. Soc. 2010, 132, 15068-15071
31. Kramer, J. R.; Deming, T. J. J. Am. Chem. Soc. 2012, 134, 4112-4115
32. Huang, J.; Habraken, G.; Audouin, F.; Heise, A. Macromolecules 2010, 43, 6050-6057
33. Sun, J.; Schlaad, H. Macromolecules 2010, 43, 4445-4448
34. Huang, J.; Bonduelle, C.; Thévenot, J.; Lecommandoux, S.; Heise, A. J. Am. Chem. Soc. 2012, 134, 119-122
35. Metzke, M.; Connor, N.; Maiti, S.; Nelson, E.; Guan, Z. Angew. Chem., Int. Ed. 2005, 44, 6529-6533
36. Schatz, C.; Louguet, S.; Meins, J.-F.; Lecommandoux, S. Angew. Chem., Int. Ed. 2009, 48, 2572-2575
37. Pati, D.; Shaikh, A. Y.; Hotha, S.; Sen Gupta, S. Polym. Chem. 2011, 2, 805-811
38. Shaikh, A. Y.; Sureshkumar, G.; Pati, D.; Sen Gupta, S.; Hotha, S. Org. Biomol. Chem. 2011, 9, 5951-5959
39. Hotha, S.; Kashyap, S. J. Am. Chem. Soc. 2006, 128, 9620-9621
40. Sureshkumar, G.; Hotha, S. Chem. Commun. 2008, 4282-4284
41. Wiejak, S.; Masiukiewicz, E.; Rzeszotarska, B. Chem. Pharm. Bull. 1999, 47, 1489-1490
42. Hanson, J. A.; Li, Z.; Deming, T. J. Macromolecules 2010, 43, 6268-6269
43. Chen, C.; Wang, Z.; Li, Z. Biomacromolecules 2011, 12, 2859-2863
44. Gabrielson, N. P.; Lu, H.; Yin, L.; Li, D.; Wang, F.; Cheng, J. Angew. Chem., Int. Ed. 2009, 48, 2572-2575
45. Morrow, J. A.; Segal, M. L.; Lund-Katz, S.; Philips, M. C.; Knapp, M.; Rupp, B.; Weigraber, K. H. Biochemistry 2000, 39, 11657-11666
46. Bhattacharyya, L.; Brewer, C. F.; Brown, R. D.; Koenig, S. H. Biochemistry 1985, 24, 4974-4980
47. Cairo, C. W.; Gestwicki, J. E.; Kanai, M.; Kiessling, L. L. J. Am. Chem. Soc. 2002, 124, 1615-1619
48. Woller, E. K.; Cloninger, M. J. Org. Lett. 2002, 4, 7-10
49. Kaltgard, E.; Finn, M. G. Application of Polyvalent Carbhohydrate Display on Virus Particles, 2009; ISBN-10: 3639201655, ISBN-13: 978-3639201659.
50. Sultan, N. A. M.; Swamy, M. J. Arch. Biochem. Biophys. 2005, 437, 115-125
51. Narahari, A.; Singla, H.; Nareddy, P. K.; Bulusu, G.; Surolia, A.; Swamy, M. J. J. Phys. Chem. B 2011, 115, 4110-4117
52. Gibson, M. I.; Hunt, G. J.; Cameron, N. R. Org. Biomol. Chem. 2007, 5, 2756-2757
53. Punna, S.; Kaltgrad, E.; Finn, M. G. Bioconjugate Chem. 2005, 16, 1536-1541
54. Mangold, S. L.; Carpenter, R. T.; Kiessling, L. L. Org. Lett. 2008, 10, 2997-3000
55. Owen, R. M.; Gestwicki, J. E.; Young, T.; Kiessling, L. L. Org. Lett. 2002, 4, 2293-2296
56. Hasegawa, T.; Kondoh, S.; Matsuura, M.; Kobayashi, K. Macromolecules 1999, 32, 6595-6603
57. Polizzotti, B. D.; Kiick, K. L. Biomacromolecules 2006, 7, 483-490
58. Gupta, D.; Cho, M.; Cummings, R. D.; Brewer, C. F. Biochemistry 1996, 35, 15236-15243
59. Swaminathan, C. P.; Gupta, D.; Sharma, V.; Surolia, A. Biochemistry 1997, 36, 13428-13434
60. Surolia, A.; Sharon, N.; Schwarz, F. P. J. Biol. Chem. 1996, 271, 17697-17703
61. Swaminathan, C. P.; Surolia, N.; Surolia, A. J. Am. Chem. Soc. 1998, 120, 5153-5159